A new palladium catalyst system for the cyanation of aryl chlorides with K4[Fe(CN)6]

被引:148
作者
Schareina, Thomas
Zapf, Alexander
Maegerlein, Wolfgang
Mueller, Nikolaus
Beller, Matthias
机构
[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
[2] Saltigo GmbH, D-51369 Leverkusen, Germany
关键词
D O I
10.1016/j.tetlet.2006.12.087
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of a novel Pd-catalyzed synthesis of (hetero)aromatic nitrites from the corresponding aryl chlorides and potassium hexacyanoferrate(II) is described. This novel protocol avoids the use of highly toxic alkali cyanides and proceeds in the presence of small amounts of palladium catalysts. High yields and selectivities of the corresponding aryl nitriles were achieved applying di(1-adamantyl)-1-butylphosphine (cataCXium((R)) A) as the ligand. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1087 / 1090
页数:4
相关论文
共 66 条
  • [1] AKITA Y, 1981, SYNTHESIS-STUTTGART, P974
  • [2] Cooperative catalyst effects in palladium-mediated cyanation reactions of aryl halides and triflates
    Anderson, BA
    Bell, EC
    Ginah, FO
    Harn, NK
    Pagh, LM
    Wepsiec, JP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) : 8224 - 8228
  • [3] TRANSITION METAL-MEDIATED REACTIONS USING [C-11] CYANIDE IN SYNTHESIS OF C-11 LABELED AROMATIC-COMPOUNDS
    ANDERSSON, Y
    LANGSTROM, B
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (11): : 1395 - 1400
  • [4] [Anonymous], 2013, ANGEW CHEM, V125, P4315, DOI DOI 10.1002/1521-3757(20001117)112:22
  • [5] [Anonymous], 2002, J ORGANOMET CHEM
  • [6] [Anonymous], ANGEW CHEM
  • [7] The development of palladium catalysts for C-C and C-heteroatom bond forming reactions of aryl chloride substrates
    Bedford, RB
    Cazin, CSJ
    Holder, D
    [J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2283 - 2321
  • [8] Catalytic Sandmeyer cyanation as a synthetic pathway to aryl nitriles
    Beletskaya, IP
    Sigeev, AS
    Peregudov, AS
    Petrovskii, PV
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (23) : 3810 - 3812
  • [9] Synthesis of 2-substituted-benzothiazoles by palladium-catalyzed intramolecular cyclization of o-bromophenylthioureas and o-bromophenylthioamides
    Benedí, C
    Bravo, F
    Uriz, P
    Fernández, E
    Claver, C
    Castillón, S
    [J]. TETRAHEDRON LETTERS, 2003, 44 (32) : 6073 - 6077
  • [10] The role of catalysis for the clean production of fine chemicals
    Blaser, HU
    Studer, M
    [J]. APPLIED CATALYSIS A-GENERAL, 1999, 189 (02) : 191 - 204